Anodic oxidation of alicyclic bromides in acetonitrile

The electro-oxidation of alicyclic bromides in acetonitrile has been investigated. Cycloheptyl, cyclohexyl, and cyclopentyl bromides each gave the corresponding N-cycloalkylacetamide and cycloalkene. Cyclobutyl bromide gave only N-cyclobutylacetamide whereas cyclopropyl bromide underwent ring-opening and yielded N-allylacetamide. The mechanism of formation of the products is discussed and the effect of concentration, temperature, supporting electrolyte, and amount of electricity consumed was studied in the oxidation of bromocyclohexane.